Working at high-end restaurants and luxury hotels might sound like a dream job, but let’s be honest, it’s often more ridiculous than glamorous. From guests ordering gourmet meals for their pet to acting like a $2,000 bottle of wine is just casual hydration, staffers have seen some truly baffling things.
So when someone online asked, “People who work in high-class restaurants and hotels, what’s the most ridiculous, stereotypical ‘rich person’ thing you’ve ever seen?”, the internet did not disappoint. Employees from around the world came forward to spill the beans, and what they shared ranges from hilariously weird to downright jaw-dropping. Scroll down for a hilarious peek into the world of the ultra-wealthy, where money talks, but sometimes it says the weirdest things. And remember, behind every ridiculous story is a hospitality worker trying very hard not to laugh (or cry).
#1
I operated a premium chain restaurant in Canada. One day this Indian gentleman started coming in, at first by himself. On the first day he spent $200 on wine and tipped $1000. The next day he did the same again. When we saw him the third time I had servers fighting over him. Anyway, one evening he got drunk on wine and Brad the busboy made the mistake complementing his watch. Mr. S. takes off his Tag and gives it to Brad. The next morning Mr. S comes back to get his car and asks if Brad is there, I say yes and go get him, Brad knows what's up and is removing the watch as he walks over to Mr. S. Mr. S says, "Brad I'm really sorry I got drunk last night and gave you my watch." Brad is chuckling as he is removing the watch and says it's no problem and he was just holding the watch until Mr. S returned. The next thing Mr. S. said, I could not believe: "Brad you don't understand, I'm sorry because it was very rude of me to give you a used gift." And at that moment Mr. S pulled out a box with a brand new Tag Heuer inside and handed it to Brad.

Image credits: alex-manutd
#2
Don't work at any high-class restaurants or hotels, but I currently live in an old yet nice and comfy apartment in Giza (around 20 minutes from the pyramids complex). The landlady is a very nice old lady, probably in her 60s, and is filthy, filthy, filthy rich.
Last year my car had to be repaired after a minor crash for more than a week, and when the landlady found out from the bawabs (doormen) about my situation, she sent one of her English-speaking maids to give me car keys for a BMW 520i, Mercedes-Benz S600, and a brand new Land Cruiser. "The madam insist you use her car until yours is repaired". I was shocked, of course, and asked her if she still could go around with her lending this much cars to me. "No worry, madam has 12 cars in al-Qahirah". Okay, I guess... I ended up only using the Land Cruiser because it's the cheapest one (I think).
Another story is when she knew I would graduate from college soon. She asked me to come visit her place, I did as she asked, and she just gave me a set of keys and some money. "Here, I have nice villa in Ain Sokhna. Go visit it with friend and family, food and drinks is on me, I have maids and cooks there. Car you can use mine, the money is for fuel. Happy graduation." I told her that I just couldn't take it, but she just shooed me away and told me to return her keys only after I really visited the villa. Haven't gone to the place yet, but I will soon enough when I have time.
Ridiculous, yeah, but in a really good way.

Image credits: ezadskoo
#3
This isn't as much a specific instance, but something that happens all the time with entitled or rich people. I work at a very expensive hotel in Hawaii and people will just come up to the desk and yell words at you. Like no hello or please, just "LUAU" or "ATM". It's like they aren't even thinking of us as people.

Image credits: maddierose1418
#4
Ordering the most expensive wine in the house...pouring two 1/2 glasses...taking a sip...and sending it back knowing full well they are paying for it.
To those folks I say THANK YOU! Nothing makes employees happier than free (expensive) booze.

Image credits: underbite420
#5
I know it may be technically off topic, but I worked IT (computer tech) in a small, tourist ski town and had a few run ins with properly rich people.
The worst was a local lawyer. Called for support because his email wasn't working. I showed up (no one at my office would take the call, but I was young and eager for work) and asked "What's the problem?"
He told me he didn't have time to explain the problem. That his time was too valuable and I should just "figure it out" because that's what he paid me for. Let me assure you, as someone that bills by the hour, I definitely made that one work.
The others are actually way more positive. Though also super-wealthy.
1) Old lady calls up, computer has a virus. Show up at her "condo." To be clear, "condo" is 4-stories, directly on the ski slope, with a private elevator and dedicated movie theater.
Computer itself is just junk though. Standard Dell crapola from 2004 or whatever. I start the virus scan and it'll take like an hour or more. Half an hour in, this little dog is yipping at me (friendly like) and the old lady picks her up, then asks how much longer. I tell her I can't really say. Scan has another 30 minutes, but if a virus shows up, it could take a lot longer to clean it up.
Old lady, Mrs. Callendar, she says "Oh, no rush, we just wanted to know if we should tell our pilot to warm up the plane yet or not."
Yeah, a $1000 PC, and my $95/hr virus scan are literally holding up a private f*****g plane. And she's okay with that.
For the record, the DOG'S name is "Marie."
And I took about 45 more minutes, and removed a minor virus, then reset her browser's settings to disable about 35 toolbars and fixed the issue.
2) Guy calls because his internet is crapped out.
Show up, typical wireless internet (directional terrestrial) for the area. Mid winter. Go climb up on the roof and hammer a bunch of icicles away from the dish antenna. Come back down, reset everything. No prob. Kids all back online.
He asks if I could help with sat-tv. I say I'd try. Basically same problem. A bit of ice, and dish needs fine-tuning on direction. Fix it, he's happy.
Leaving, he tries to give me cash. I say we bill through the company, but if he has a business card or something, that's easiest. He says, "Yeah, but don't bill the company, I'll write my personal on the back."
Get card, thumb covers part of it. Card says "PepsiCo." Read "President" near my thumb. Expect to move thumb, see "of Western Marketing" or something. Nope. Says: "And CEO."
(Super secret, business card had a coupon on the back. Good for one frito-lay or pepsi soda product, or 75¢ off anything else from PepsiCo.)
3) Guy calls our local repair shop (only one for 100+ miles) asking if we install routers. Sure, yeah. "Do you sell computers?" Yeah, those too. "Well, I'd like to buy... (he counts on fingers or something) Like 5 PCs, one for each room, and 3 or 4 laptops to throw around the place."
This is like $30k sale in a shop that typically does $1000/week in sales tops. Check with boss. He says get credit first. Guy insists he can pay cash, but I should bring it all to his new house next week.
Credit goes through. Show up at mountain mansion. 6000 sq. ft. Entire flat-bed truck of empty wine crates, straw spilling out of their wooden slats.
Go to unload, old, chubby guy walks up in sandals and cargo shorts. "Hey, are you the computer guy?"
"Yeah, that's me." Look at guy, assume he's property manager/butler/cousin/something. "I'm looking for Mr. XXXXX"
"Oh, that's me. Here, let me give you a hand with those boxes."
He helps unload, shows me the place, thanks me profusely for showing up on such short notice, etc. Turns out he was retiring from a CFO gig at a major company in Chicago.
In the process of installing things, I saw the full house. Wine cellar alone was huge. 18 ft. ceilings with a rolling, library-style ladder on a half-moon shelf of wine. Connected directly to that was a walk-in humidor. Outside of that, a massive media/theater room. The whole house was connected to a smart-home system that juggled a DVD jukebox (this was before streaming) to every TV in the house, complete with 12" touchscreen tablet "remotes" that, when carried, would cause the show to follow you from room to room, opening and closing hidden screens, curtains, and activating/dimming lights. Insane, and yet, the guy was super friendly.

Image credits: Xepher
#6
I am a cocktail server at the huge pool of a 4 star hotel. A woman said in a mono-tone voice and without any eye-contact "I lost my sunscreen. Find it.".

Image credits: bluebunny20
#7
Ordering $150 caviar to-go for their cat.

Image credits: zhougdog
#8
Worked at a grocery store in uppity Gold Coast Chicago when I was a teen.
We sold soup for lunch and when bagging them, we put it in a paper bag followed by a plastic bag to make sure it’s secure.
Lady buys a soup, I proceed to bag the soup and she says no, I’ll just put it in my bag.
I say, M’aam are you sure?
Mind you she has a Louis Vuitton bag that looks brand spanking new.
15 minutes later she comes in raging that she has minestrone all over her Louis Vuitton and demands to speak to a manager. Smh.

Image credits: jkeemi
#9
Oh yay, I love this one. First and foremost, throw a 6 year old's birthday party at a tapas restaurant called "______ Wine Company." Try to feed them tartare. Scoff when your child asks for balloons or French fries. Try to feed them jalapeno creme brulee for dessert. Try to quiz them on picking out scents in wine. Sigh when they don't care. Keep ordering more wine when they fall asleep on the booth. Complain to in-laws about how exhausting motherhood is. Have to Uber home with a six year old. Everyone else:
Order a walnut salad and then yell at your server for it having walnuts, because you're allergic.
Yell at server because the top of the creme brulee is... Burnt.
Inquire about the immigration status of the chef.
Tip your server $40 immediately after telling her she "doesn't look too bright," tell her she'll get over it.
Shove your server when he comes to warn you that your reservation on the table is officially past the previously agreed upon time. Scream that he isn't allowed to touch you back when he tries to disconnect your arm from his collar.
Edit: these were all different people.

Image credits: Wolf_Craft
#10
I don't even work at that nice of a restaurant, but last month I got chewed out over the phone because some lady left her baby's actual silver spoon on the table, and we didn't know where it was so obviously one of us had stolen it.

Image credits: startush
#11
I’ve got a pretty good one! I work at a luxury property in California, and we had the co-founder of a large payment processing company stay with us a while back. He only liked to sleep on his own bed, so when he woke up that morning, he paid a team to load his bed into a truck and have it delivered to our property. We then removed the bed in his luxury suite and setup his bed that his team had brought us. He only stayed with us one night and the process was done to send the bed back home the following day. It kind of blew my mind that he went through all that trouble, just so he could always sleep on his own bed. To each their own, I guess!

Image credits: Techno_Wasp
#12
Late to this party but I have a positive one to throw in amidst all the negative.
I'm loosely aquainted with someone who is obscenely rich. He dated my best friend for a while back when we were in college. As you can imagine, he bought her fancy things all the time, took her on expensive family vacations with his folks, ect ect. He was a stereotypical rich kid, but he was also kind and still very down to earth.
They dated about a year and in the spring we went spring breaking in his family's condo at a famous spring break beach location and there was just me, my best friend, him and a couple of his friends. The group decided we wanted good old fashioned Waffle House breakfast after a night of revelry. After eating, I noticed he was lingering behind the group. He'd said he had to take a leak, but he stopped back by the table on his way out to the car. Curious, I ran back to the restrooms just so I could pass by the table to see what he'd done.
He left the waitress a small pile of Benjamins as a tip. Had to be 4 or 5 hundred dollars. I couldn't quite tell because they were folded and rumpled from being in his wallet.
My mouth fell open when I saw it and I forgot I was even heading to the restroom. I looked out by the car and he was watching me through the glass windows, held up his finger to his lips mouthing, "shhhh," and beckoned me back out to the car.
I didn't tell, but my eyes were glued to the table as we pulled away in his car. The waitress collapsed into the seat of the table when she saw it. Pretty sure she was crying.
Letting that guy get away was the dumbest thing my best friend ever did in her life.

Image credits: WifeyP
#13
My former boss (insanely wealthy), used to stay in presidential suites and would have any and all red removed. He was a high roller at several casinos and they made special chips just for him as a substitute to red chips. He hated the color red because when you’re losing money, you’re “in the red.”.

Image credits: anon
#14
I play poker for a living and every now and then some rich guy will sit down and start going all in every hand for $300-500 without looking at his cards.
One day I was in a game where a guy was betting $1000-3000 dollars without looking at his cards. It was insane to me but for him I guess it wasn’t that much money.

Image credits: badreg2017
#15
I worked for a resort in the Seychelles for 4 years. I have hundreds of stories which would fit this post but one that stands out was a very wealthy Canadian family who stayed at one of the private residences for a couple of weeks.
They brought their own staff including two personal chefs but also asked for a hotel chef to assist their team with prep and local ingredient knowledge. A chef I was friendly with was selected to spend the two weeks with them.
One day, another member of their staff came down to one of the restaurants and purchased two bottles of wine for €11,000+ each. Now we had far more expensive bottles on the list but this was still a notable sale and later that night, I asked my mate what they had cooked to accompany the wine.
Turns out they had poured both bottles into the pot while making a Coq au Vin.

Image credits: diarm
#16
So I’ve played at a lot of these venues with rich clientele, but the one that takes the cake is the rich cockwaffle that comes and demands we play [Insert Pop Song on the No. 10 Billboard] because his little princess likes it. Now while we have taken requests before, what’s difficult here is that my fellow colleagues and I, professional string musicians, are getting paid by the venue to play classical music. That we have pre-agreed on and prepared. My colleagues and I do not know the melody nor harmony nor even the bloody key of generic pop song No. 7. Not even that, but we are not getting paid by you or your “little princess”, so we aren’t gonna play it. Not that this makes us exactly...loved by some of the venues patrons.

Image credits: AngryPuff
#17
I interviewed at a large hotel attached to a casino and while I was being shown around the front desk, a woman walked up, said nothing, and got room keys after being greeted by the front desk agent. She immediately turned and walked away. Then the manager who was interviewing turned to me and said, “That’s Mrs. Richladypants. You never ask her for her name, her ID, or god forbid a credit card. She stays here comped once or twice a week because her husband spends so much in the casino. If you upset her she will yell at you and then hand the person working next to you a $100 bill just to spite you.”
I ended up turning down a job there, thankfully so because apparently she wasn’t the only guest of her type there.

Image credits: arnber420
#18
My uncle works at a very upscale restaurant on a very well-to-do and desirable vacation island in the Atlantic Ocean.
One of their regular customers is a billionaire oil guy. My uncle has told me:
* he arrives on a yacht that tows a smaller yacht. The smaller yacht is still big enough to have a helicopter.
* he demands to have his dogs seated at the table and feeds them foie grass and expensive water.
* when he takes humans to eat my uncle has never seen him with the same woman twice, and often it’s a table of women.
* if he really liked the meal he will go through the restaurant and, in front of everyone, peel off crisp 100s from a giant roll of money in his pocket and tip every service person whether they helped or not.
* one time the owner got a call from health inspectors saying they received a complaint that dogs were seen eating in the restaurant. All the owner did was speak the billionaires name and the health inspector said, “Oh okay, bye.”.

Image credits: Auto_Fac
#19
TL;DR: Average snobby rich people, but also many celebrities were encountered with a mix of good and bad experiences including Jenifer Aniston and Michael Ian Black.
I used to be the head host and event manager for a very popular and swanky restaurant in Austin, Texas. For the most part they were quite civil and in no way demanding for special accommodations (the owners of the restaurant required us to notify management in order for them to get special treatment however). They clearly did not want to make a fuss about being there and what not. Regarding generic rich people, it was never quite that bad, although I did have one guy slip two $100 bills at different times in order to move up the waiting list faster, and another couple who came in to eat before heading next door to ACL to see Jack White. It was a weekend night at 6:30, our busiest time, and I informed him it would be a 2 to 2.5 hour wait. He immediately got agitated and started to go on about how he had tickets to the show and needed to be seated immediately and at this point I can tell he has already had way too much to drink. I pointed out to him that pretty much everyone in the restaurant was pretty much doing the same and they made reservations. He got angrier with me because he had called earlier trying to make a reservation. We don’t take reservations for the current day after 5 pm so he was lead to believe I lied to him and asked for my manager and begin to berate and insult me in front of all the other guests. Luckily the no nonsense manager was on duty and asked him to leave and while doing so took one of our chairs outside the entrance and through it into oncoming traffic.
We also got celebrities on a weekly basis in the summer time and during ACL and SXSW.
Two instances in particular stand out the most. One with Michael Ian Black and the other with Jennifer Aniston
MIB:
Upon his entering I didn’t realize it was him at first, and we were required to ask for both First and Last name from the head of the party in order to put them into the Open Table system. The reason why was to ensure we knew exactly when and for how long they were seated and who their server was in case they called back with complaints or the occasional praise.
Anyway in walks MIB and after asking him for his name his just snaps immediately at me exclaiming that I don’t need his name. I apologize and explain, and at this point I just label them as guest X, but he proceeds to think I was explaining in order to still receive his name. I then inform him there is a slight wait and he then gets annoyed even more and points out there are several empty booths. I tell him those are for reservations within the next hour and unfortunately I can’t seat him there. I direct him to the bar while he waits. I get to seating him and begin to tell him about the restaurant as I’m supposed to do and he just snaps that he and his guest would like to not be bothered. For the rest of his visit, he was rude to several servers and food runners, and unnecessarily condescending concerning his order. I don’t quite remember what tip he left, but it was subpar. Even more so based on the fact I sat him in one of the best servers in the restaurant. I just wanted to go up to him and tell him not to worry about us calling paparazzi and informing them he was there because 1. I’d get fired immediately, and 2. They literally would not give a flying f**k lol
JA:
Now to anyone who is worried here, Ms. Aniston was not the rude one, in fact she was quite friendly. Earlier in the day I get a call from this woman wanting to make a reservation for 8 (no problem, it was the same day as the woman’s World Cup so we were really slow) and she wants a table by the window which was also not a problem. However then she proceeds to demand that no other parties be seated at any tables directly next to them for the duration of the meal. I explain to her I’ll try my best to accommodate this, but in no way can I guarantee it if more guests show up than is possible to reach that goal. She. Goes. Off. She starts telling me I better do this because the table is seating several high profile people and that they demand they have this demand met. I ask who the people are and she will not reveal information because I’ll call the paparazzi. I’d also like to add, I don’t have a f*****g clue how I would even go about doing that. Anyway they show up and I realize it is Jennifer Aniston, as well as Jason Bateman, Sia, and Sandra Bullock (she wasn’t as exciting to see because I had seen her multiple times in Austin over the years and got to meet her while eating at a restaurant she owns. They were absolutely the nicest people. Incredibly friendly. They even allowed for the employees to take a few pics after the meal. But the best part was when the assistant to Ms. Aniston, the woman on the phone, was finally seated, she had to eat at the bar by herself and was not included.

Image credits: anon